Top Arezzo Sightseeing Tours

Discover Cortona, the town made famous by the novel Under the Tuscan Sun, during a prvate walking tour. With a local guide, you’ll hear fun facts about the book and the film as you stroll through the Roman square of Piazza della Repubblica and see landmarks such as Teatro Signorelli and the Palazzo Comunale. Choose between a morning or afternoon tour when you book.

You will visit with us our winery and vineyard to discover our philosophy and passion. A unique experience in which you can then taste 4 wines from Villa La Ripa, paired with excellent products from the Tuscan tradition in a light three-course lunch. You can also enjoy a wonderful view from the tasting room overlooking the winery and the vineyards of the company.

Discover Cortona on a private, fully curated luxury e-bike journey blending breathtaking Tuscan landscapes, culture,and authentic local experiences.Ride premium e-bikes along serene, scenic routes with a professional local expert who brings the region to life with stories, history, and insider knowledge far from crowded paths.Pause to admire charming corners and hidden views, feeling the rhythm of the rolling hills and medieval streets. The journey culminates at a refined, private winery where the owner welcomes you for a curated Tuscan lunch with no overlapping. Savor seasonal appetizers highlighting the finest local products, a thoughtfully prepared first course, dessert or gelato and coffee,paired with at least three glasses of Syrah from different vintages to reveal depth and character.Designed for couples, families, and discerning travelers, this is a seamless, immersive, and unforgettable way to experience Cortona—where every detail is crafted for comfort, privacy, and discovery.

Discover the charm of Pienza at your own pace with a self-guided walking tour that combines exploration, learning, and interactive fun. This 1-hour tour covers a scenic 1.5 km route through the historic center, a UNESCO World Heritage Site, starting from the iconic Pienza Cathedral. Engage with the city’s fascinating history through audio guides and quizzes, making learning enjoyable and competitive. Whether you’re solo or with friends, Pienza’s beautiful streets and rich stories await you. No need for a group; enjoy the freedom to explore when you want. - Self-guided tour allows for a flexible schedule - 1.5 km walking route with a duration of about 1 hour - Interactive quizzes to enhance your experience - Available daily in multiple languages, suitable for all ages

Discover Arezzo your way with Ciceru’s self-guided walking tour—audio and text in 7 languages, right on your phone. No app, no hassle—just press play and explore! Walking through the streets of Arezzo is like stepping back in time. Be enchanted by the frescoes of Piero della Francesca, the grandeur and splendour of the Duomo and the wonder of Piazza Grande. Arezzo is the ideal destination for a short trip between nature, art and good food!

Discover the iconic Tuscan town of Cortona (made famous in the book by Frances Mayes "Under The Tuscan Sun"). Located between Florence and Rome, Cortona is rich in Etruscan roots. Cortona is an easy city for everyone to really love. This is because of its atmosphere, its Etruscan past, its delightful medieval old town and also its splendid panoramas.

This is not simply an e-bike tour — it is a curated private experience for travelers who value authenticity, comfort, and true local elegance. Set among the timeless landscapes of the Val di Chiana and Cortona, the journey unfolds at a relaxed pace, allowing you to connect deeply with the territory rather than simply pass through it. Carefully selected panoramic routes avoid crowds, offering breathtaking views, silence, and the true rhythm of Tuscany. Effortless riding is ensured by premium-quality e-bikes with all modern comforts, while your **certified local guide** shares authentic insights, history, and storytelling, offering a genuine perspective of the region with refined attention to detail. Designed for couples, families, and discerning travelers seeking privacy and quality, this is an intimate and elevated way to discover Cortona — immersive, seamless, far removed from ordinary group tours, and tailored for each guest

Embark on a private, guided journey through the picturesque vineyards and historic cellars of Montepulciano, the home of the celebrated Vino Nobile di Montepulciano. This exclusive tour offers an immersive experience that captures the essence of Tuscan winemaking tradition. What to Expect Guided Visits to three renowned Wine Estates: Explore estates with centuries of winemaking expertise. Learn about the intricate process of crafting Vino Nobile di Montepulciano from passionate experts. Exclusive Wine Tastings: Savor a curated selection of exquisite wines at each estate. Lunch at the Second Estate: Indulge in a traditional Tuscan meal paired with exceptional wines. This intimate experience blends Tuscan culture, history, and gastronomy into a memorable day amidst the stunning countryside of Montepulciano. Whether you're a wine enthusiast or simply looking to enjoy a luxurious day in Tuscany, this tour is the perfect choice.

Take a real sip of Tuscany's chill and calm countryside and escape the busy pace of Rome. Come and savor the very best of the Tuscan countryside—its flavors, stories, and breathtaking views. Exclusive & Intimate: Small-group experiences (max 7 per guide) ensure personalized attention and genuine local interactions. Unforgettable eBike Rides: Explore ancient paths, scenic vineyards, and breathtaking landscapes on high-performance pedal-assist bikes. Culinary Immersion: Savor authentic Tuscan flavors through unique dining experiences—from a hillside cheese house picnic to a hands-on cooking class and intimate restaurant dinners. Cultural Insights: Engage with local experts who unveil the hidden stories and history of this iconic destination. Book now for a once-in-a-lifetime adventure through Tuscany—a journey that delights your senses and nourishes your soul! Contact Us: For more detailed information or to receive a discount code for your booking, please contact us before booking.

This e-bike tour starts from the historic center of Citta' di Castello, to reach Montone classified among "Most Beautiful Villages in Italy". The approximately 45 km long route can be tackled by all people with basic level of supported training of our pedal assisted bikes. We will follow the banks of the Tiber river a totally traffic-free path until we climb the gentle hills that lead to Montone. Here you leave your bikes we will discover the medieval village with a suggestive view of the Tiber Valley. On request it will be possible to visit the Montone Museum inside the magnificent Cloister of San Francesco where paintings and art objects from the history of Umbria are kept. After the visit we will take the Tiber cycle path back to the starting point in Citta' di Castello

A tour where you can appreciate the beauty of the Umbrian High Tiber and its traditions. You will have at your disposal brand new e-bikes with which you can reach a local winery specialized in the production of "vinosanto". A licensed National Guide will lead the tour in Italian or English presenting the most interesting aspects of the historical and natural heritage of the valley. We will cross the historic center of Citta 'di Castello to follow the pleasant cycle path of the Tiber river until we arrive in the countryside where the winery is located where we will taste the "Vinosanto".

I was Born and raised in this magical region od Tuscany, I have key villagers that I have known for many years and you know in Italy is all about relationships...I go above and beyond to take care of my clients. One thing that makes me unique is that I have lived abroad for several years and my spoken English is excellent, this is very important for you to maximize your tour and investment, I comunicate well and I know how to relate to the culture overseas. One other thing is I can sure teach you history but what my clients love about me is the stories and secret I tell them and one thing is for sure...you will laugh and not be the usual boring tour!!!!!

See Tuscany’s loveliest scenery, and discover the history of one of Italy’s most revered wines, on this private, half-day tour. Following pickup from your area hotel, head off the tourist trail to a local, family-owned winery. Taste Brunello di Montalcino—a 100% Sangiovese wine that’s one of Italy’s best—as well as other wines and nibbles. You’ll also tour the idyllic Val d’Orcia, from ancient hill towns to historic monasteries.

Brunello di Montalcino is one of Italy's most prestigious wines, but navigating to the rural wineries outside of Montalcino on your own can be stressful. On this private wine tour, let your driver take the wheel and focus on vineyard views as you make your way to the top wine estates and cellars for exclusive tasting experiences. Explore stunning vineyards, learn about traditional winemaking techniques, and savor the rich flavors of Tuscany with guided tastings and a traditional lunch.

Discover Lake Trasimeno on a 5-hour guided e-bike tour, perfect for nature and culture lovers. Ride along a cycle path nestled among centuries-old olive groves and woods, reaching the picturesque San Feliciano pier for a short boat ride to Polvese Island. Here, explore the 13th century Castle and the ruins of the monastery. Relax on one of the equipped beaches, enjoying the traditional Torta al testo and a good local wine. - Guided tour of 56 km, suitable for groups of 4 - 8 people - Includes e-bike and helmet rental - Possibility of Wine Tasting and Typical Products by Reservation

Walking through the medieval streets of Arezzo is a unique experience. Tradition, history and beautiful landscapes to photograph. Arezzo offers all this and much more. The tour aims to show the truest Tuscany, far from the classic tourist routes. Booking a day in Arezzo allows you to relax in one of the most beautiful medieval cities in Tuscany.

Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore Piazza del Campo, famous for the Palio di Siena horse race, admire the breathtaking Duomo (Cathedral), and wander through the charming, narrow streets of the historic center. Wine Tasting & Light Lunch Next, we’ll head to a renowned winery for a light lunch paired with an amazing wine tasting experience. A sommelier will guide you through five exceptional wines, plus an olive oil tasting. After lunch, we’ll continue our journey with a spectacular drive through the rolling Vernaccia di San Gimignano vineyards, home to Tuscany’s most famous white wine. Stop in San Gimignano you’ll have free time to explore this medieval gem, known for its 14 towers dating back to the 13th century. The town’s atmosphere will transport you back to the Middle Ages! And of course, you can’t miss the world’s best gelato at Gelateria Dondoli.

Experience the magic of Tuscany without the sweat! Join us for a half-day e-bike adventure through the rolling hills surrounding the “Ideal City” of Pienza. This tour is carefully designed to take you along the most iconic white roads (strade bianche) in the region, offering panoramic views that look like they’ve been pulled straight from a postcard. Tour Highlights: Effortless Riding: Glide up the Tuscan hills with ease thanks to our premium electric bikes. Iconic Landmarks: Cycle past the famous Gladiator Row (Cipressi di San Quirico) and the charming Vitaleta Chapel. Cinematic Views: Capture the breathtaking landscapes of the Val d’Orcia, a UNESCO World Heritage site. Local Culture: Start and finish in the Renaissance gem of Pienza, with plenty of tips on where to find the best Pecorino cheese or best restaurants.

During this 2-hour private tour, your expert guide will lead you through the most important and interesting sites of the beautiful city of Arezzo. You will be able to admire the medieval city and visit its historic shops.

Tuscany is famed for its scenery and gastronomy, but navigating this rustic region isn’t easy—especially for first-time visitors. Enjoy a deluxe introduction to the rolling Tuscan landscape during this full-day tour of Cortona and Montepulciano. A heart Tuscan lunch is included, plus a guided tour of a historic wine cellar and five exclusive wine tastings.

This exclusive private wine tour takes you from Cortona to the heart of the Chianti Classico Black Rooster, an iconic wine area rarely reached from this part of Tuscany. Travel in comfort with a local professional driver and enjoy a personalized journey through one of Tuscany’s most celebrated wine landscapes. The experience includes visits to three carefully selected Chianti Classico DOCG wineries, where you will enjoy guided cellar tours and premium wine tastings. Each winery offers a different perspective on the Black Rooster tradition, allowing you to discover the diversity, history, and craftsmanship behind authentic Chianti Classico wines. A traditional Tuscan lunch is included, perfectly paired with local wines and seasonal products, for a complete and immersive Chianti experience. Designed for travelers seeking authenticity, privacy, and high-quality wine experiences, this tour combines culture, scenery, and exceptional flavors in a relaxed and exclusive setting.

Arezzo is famous because Giorgio Vasari was born here, the disciple of Michelangelo, who designed the famous Uffizi and the Vasari Corridor in Florence on behalf of Grand Duke Cosimo I De' Medici. Our tour's principal stops are as follows: The city's center square, Piazza Grande, is uniquely typical with its porticoes dating from the sixteenth century. Piazza del Duomo: this stunning medieval structure, dominating the plaza, houses priceless artwork by Donatello and Piero della Francesca. Arezzo's ancient lanes and streets, where the ambiance of the old goldsmith shops is still palpable. The most well-known painting by 15th-century painter Piero della Francesca is located in the Basilica of San Francesco, Cappella Bacci. Based on the advice of Dominican priest Jacopo da Voragine, these frescoes tell the story of the True Cross! How could anyone possibly miss a tour this thorough? Now let's move!

Take a break in the countryside with a private tour that includes visits to boutique wineries and a sustainable, family run cheese farm. Enjoy a full day dedicated to wine and cheese, exploring the heart of Tuscany. Drive through the Val d'Orcia, a UNESCO World Heritage Site, and savor some of the region’s finest red wines, including Vino Nobile di Montepulciano and Brunello di Montalcino. Stroll through the medieval squares of Pienza and sample authentic Tuscan cheeses at a historic estate, featuring one of the most breathtaking terraces overlooking the Orcia Valley.